The Voyageurs Cup was first conceived in March 2002 by fans of the Canada men's national team, known as the Voyageurs, following Canada's surprise success at the 2000 Gold Cup. After years of being promised a domestic Canadian cup by the Canadian Soccer Association (CSA), the Voyageurs took it upon themselves to commission a national trophy using member donations. Veteran Voyageurs member and chief fundraiser since the group's founding in 1996, Dwayne Cole, solicited donations on the Voyageurs internet forum, resulting in $3,500-$4,000 donated. The money was used to commission the trophy, made in Winnipeg, Manitoba. The cup itself is a handled wine cooler made from solid brass and electroplated in sterling silver. The base is lacquered, solid Canadian Oak and set with die cut polished aluminum maple leaf annual plates. An accompanying solid oak case was also crafted for safe transport.[citation needed]

Statistics for Montreal Impact include the original Montreal Impact of the USL and NASL, who contested the trophy from 2002 to 2011, before being replaced by a new MLS franchise of the same name and ownership.

Statistics for Vancouver Whitecaps FC include the original Vancouver Whitecaps of the USL, who contested the trophy from 2002 to 2010, before being replaced by a new MLS franchise of the same name and ownership.

The inaugural Canadian Championship was held in 2008, with the three Canadian teams spread across MLS (Toronto FC) and the USL First Division (Montreal Impact and Vancouver Whitecaps) each playing four non-League games in a round robin format.

^The format of the 2011 tournament was different from previous editions. In 2011, with four teams involved, the tournament was changed to be a home-and-away semi-final round and a similar final round between the winners. Toronto, as reigning champions, were assigned the top seed and were matched with Edmonton, which was assigned the fourth seed as newcomers to the tournament. The two remaining teams, Montreal and Vancouver, faced off in the other semi-final.[4][5]